Professional athletes can make millions of dollars through lucrative contracts — and sometimes billions when you add in endorsement deals — but despite their high paychecks, many end up going broke. According to a 2009 report by Sports Illustrated, 78% of former NFL players have gone bankrupt or are under financial stress within two years of retirement, and within five years of retirement, an estimated 60% of former NBA players are broke. Similar fates have befallen professional baseball, golf and hockey players as well.

But where exactly do those millions go? GOBankingRates is breaking down exactly how 25 athletes lost millions of dollars, with some falling from the top of their game to financial rock bottom.

Last updated: Feb. 6, 2020

1/25

Jim Prisching/AP / Shutterstock.com

Lance Briggs: Lost His $2.3 Million Illinois Mansion

Former Chicago Bears linebacker Lance Briggs spent 12 years playing in the NFL, retiring in 2015. Back in 2008, Briggs paid $2.3 million for a six-bedroom, 5,158-square-foot, English-style mansion in Northfield, Illinois, but lost it after his lender foreclosed on it in 2017, the Chicago Tribune reported. Briggs also owned a townhouse that went into foreclosure that same year, Crain’s Chicago Business reported.

The mansion was sold in January 2020 for $1.1 million — less than half what Briggs had purchased it for.

2/25

Paul Sancya/AP / Shutterstock.com

Clinton Portis: Lost $3.1 Million Due to Bad Financial Advice

Former Washington Redskins and Denver Broncos running back Clinton Portis signed an eight-year, $50.5 million contract in 2004, which at the time made him the highest-paid running back in NFL history, Sports Illustrated reported. But Portis filed for Chapter 11 bankruptcy and was basically broke by 2009. Portis told Sports Illustrated that trusting the wrong people was a major contributor to his financial downfall. His financial advisor, Jeff Rubin, got him to invest $1 million in an Alabama casino that was shut down in 2012 after the state’s regulators got involved. Portis told the magazine that a total of $3.1 million from his account was taken by Rubin.

“The complication begins because you don’t understand it,” he said. “You don’t know what they’re saying, but you just get involved.”

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3/25

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Michael Vick: Lost $3.75 Million Due to Illegal Dogfights

When former NFL quarterback Michael Vick pleaded guilty to federal charges relating to an illegal dogfighting operation, the Atlanta Falcons sought to recover nearly $20 million in bonus money they had paid him between 2004 to 2007. The Falcons argued that Vick had used the money to finance his illicit activities. In 2008, a judge ruled that he could keep all but $3.75 million of the bonus money, ruling that recovering all of the bonuses would violate the NFL collective bargaining agreement, ESPN reported.

Vick ended up filing for bankruptcy in 2008, but by 2017, he had paid back $17.4 million of the $17.6 million he owed creditors. He was able to make the money back after rejoining the NFL and later working as a studio analyst for Fox Sports following his stint in prison.

4/25

AP / Shutterstock.com

Johnny Unitas: Lost $4 Million on an Investment in a Circuit Board Company

Former Baltimore Colt quarterback Johnny Unitas made a bad investment that landed him in bankruptcy court. The NFL player filed for Chapter 11 bankruptcy in 1991 after his bank attempted to collect on nearly $4 million in failed loans made to Unitas and his business partners in the mid-1980s for the purchase of a circuit board manufacturing company, The Baltimore Sun reported. According to Forbes, Unitas and his partners purchased National Circuits for $3.5 million in 1994, and six years later, they could only sell it for $1 million.

5/25

Anonymous/AP / Shutterstock.com

Jack Clark: Racked Up $6.7 Million in Debt With His Penchant for Fancy Cars

Former Boston Red Sox player Jack Clark — nicknamed Jack the Ripper — played in the MLB from 1975 to 1992 and filed for bankruptcy that same year, citing $6.7 million in debt. It’s likely his affinity for luxury cars landed him in the hole — his bankruptcy filing stated that he owned 18 cars, including a $717,000 Ferrari, Sports Illustrated reported.

6/25

AP / Shutterstock.com

Bryan Trottier: Racked Up $9.5 Million in Debt With a Failed Ice-Rink Business

Six-time Stanley Cup championship winner Bryan Trottier declared bankruptcy in 1994, with less than $150,000 in assets and nearly $9.5 million in debts. Some of those debts were owed to investors in his ice-rink business, BT Skating Corp., which went into foreclosure, The New York Times reported.

7/25

Mark J Terrill/AP / Shutterstock.com

Evander Holyfield: Lost His $10 Million Mega-Mansion

Boxer Evander Holyfield was once the proud owner of a 109-room, mega-mansion in suburban Atlanta, but the home was repossessed by the bank after he failed to make payments on his $10 million home loan, CNBC reported.

The house was eventually sold to rap mogul Rick Ross for just a fraction of what it cost Holyfield. The property was originally listed for $8.5 million but sold for less than $5.9 million, Redfin reported.

Luther Elliss: Lost $11.6 Million Due to Failed Investments and Overspending

Luther Elliss played 10 years in the NFL and made $11.6 million in one five-year span. But in 2010 he was relying on help from his church friends to pay his bills and even afford food, the Deseret News reported. He filed for bankruptcy in 2009 with a number of things attributing to his debt, including a $1.6 million mortgage loan and overspending on cars and jewelry. However, Elliss told the Deseret News that poor business decisions were the biggest culprit in his multimillion-dollar loss.

“Most of it was bad investments, good money chasing bad money, trying to save it instead of cutting your losses,” he said. “I’m not one to give up too easily on things, so it was always just a little bit more, a little more time, a little more money and before we knew it, I put up the houses and guaranteed the loans, and when that came due, the bank came knocking on my door.”

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9/25

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Dan Marino: Lost Over $13 Million on an Investment in the Company That Created the Tupac Hologram

Former Dolphins player and NFL analyst Dan Marino had a big stake — to the tune of 1.6 million shares — in Digital Domain Media Group, a digital production company founded by James Cameron that produced the digital effects for “Titanic” and “Transformers,” as well as the Tupac hologram that appeared at Coachella. His investment, which was once worth $14 million, dropped down to a value of $850,000 after the company declared bankruptcy, Sports Grid reported.

10/25

Markson Sparks / Shutterstock.com

Mike Tyson: Racked Up $13.4 Million in IRS Debt

Former heavyweight champion Mike Tyson earned about $400 million over 20 years in and out of the ring, but he squandered his wealth with lavish spending on everything from jewelry to Siberian tigers, The New York Times reported. In 2003, he filed for Chapter 11 bankruptcy stating that he had racked up $23 million in debt. Included in that debt was a whopping $13.4 million he owed the IRS.

11/25

Uncredited/AP / Shutterstock.com

Bernie Kosar: Lost $15 Million Because He Put Too Much Trust in Friends and Family

When quarterback Bernie Kosar signed a $6 million contract with the Cleveland Browns in 1985, he entrusted his father to take care of his money. Kosar has said that his father used Kosar’s signing bonus to pay his own mortgage and buy cars. According to the book “Is There Life After Football?” Kosar ended up losing $15 million between his father’s mismanagement of his funds, loans he gave to friends and family that were never paid back and bad investments he made that were spearheaded by friends and family.

12/25

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Floyd Mayweather: Racked Up $22.2 Million in IRS Debt

Mike Tyson isn’t the only boxer who ended up owing the IRS millions. Floyd Mayweather may call himself “Money,” but he didn’t have enough of it to pay the IRS what he owed in taxes — at least that’s what he claimed in response to a lien the IRS issued in 2015, Deadspin reported. Despite earning $200 million for a single fight, Mayweather asked the IRS for an extension to pay back the $22.2 million he owed them in taxes for the year.

13/25

Ann Heisenfelt/AP / Shutterstock.com

Vince Young: Lost $25 Million Through Negligence and Irresponsible Spending

NFL quarterback Vince Young signed a lucrative $25 million contract with the Tennessee Titans, but just seven years after he inked that deal he filed for Chapter 11 bankruptcy, Sports Illustrated reported. According to court documents obtained by the publication, Young’s assets totaled between $500,001 and $1 million, while his total debt was between $1,001,000 and $10 million.

Young said he didn’t pay attention to where his money was going throughout his career, trusting his financial advisor and his uncle to make decisions for him. He was also generous to a fault, purchasing one relative two cars, building a house for his mom and treating his teammates to a $15,000 meal at the Cheesecake Factory.

14/25

Matt Slocum/AP / Shutterstock.com

Jack Johnson: His Parents Spent His $30.5 Million Salary Before He Even Got It

NHL player Jack Johnson signed a seven-year, $30.5 million contract with the Columbus Blue Jackets, but was left with nothing and forced to declare bankruptcy after his parents mismanaged his funds. According to court documents, his parents took out loans against his future earnings, including at least $15 million across 18 high-interest loans that resulted in multiple defaults. His parents also allegedly purchased a beach house in California, bought cars and paid for travel to see him play, Forbes reported. Johnson was not aware of all the purchases made in his name and was sued several times for defaulting on loan payments.

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15/25

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Warren Sapp: Spent His $40 Million Fortune on Shoes, Watches and a Lion-Skin Rug

Warren Sapp played in the NFL for 13 years, making an estimated $40 million over the course of his career, Bleacher Report reported. Not only did Sapp spend his fortune, but he ended up $6.7 million in debt, according to a bankruptcy filing he made in 2012. Overspending seems to be the cause of Sapp’s financial downfall — a list of his assets included 240 pairs of Jordan shoes worth over $6,000, a watch worth $2,250 and a lion-skin rug worth $1,200.

16/25

David Zalubowski/AP / Shutterstock.com

Mark Brunell: Sunk $50 Million in Failed Businesses

Former NFL player Mark Brunell lost the $50 million he earned throughout his career by putting it into failed businesses. Action News in Jacksonville, Florida, reported that he invested his money into nine businesses and enterprises, five of which went bankrupt. One of Brunell’s biggest financial losers was a company called Champion LLC, which purchased high-end investment properties. When the real estate market crashed, Brunell lost everything he had put into the company and ended up owing even more due to the loans that had been taken out to buy the properties.

John Daly: Gambled Away $50 Million

Golfer John Daly loves to gamble, a hobby that’s cost him millions. Daly told ESPN that he did the math on the shocking amount he’s lost: “I lost about $98 million and won about $45 million gambling. So yeah I lost around $50 million,” he said, according to USA Today.

18/25

Steven Senne/AP / Shutterstock.com

Curt Schilling: Lost $50 Million on a Gaming Company Investment

MLB pitching great Curt Schilling invested more than $50 million of his career earnings into his video game company, 38 Studios, and lost it all when the company declared bankruptcy in 2012, ABC News reported.

“The money that I had earned and saved in baseball was all gone,” he told radio station WEEI-FM. “I put everything in my name in this company. I believed in it. But I’m not asking for sympathy. That was my choice.”

19/25

Julie Jacobson/AP / Shutterstock.com

Sheryl Swoopes: Lost $50 Million Due to Bad Representation and Bad Investments

Although WNBA salaries topped out at six-figures when Sheryl Swoopes was in the league, she was able to make $50 million during her basketball career thanks to a lucrative Nike contract. Unfortunately, she lost it all due to a series of bad investments and poor money management by her lawyers and agents, Money reported. She filed for Chapter 13 bankruptcy in 2004.

20/25

Chris O'Meara/AP / Shutterstock.com

Lawrence Taylor: Lost $50 Million Due to Hard Partying and Drug Use

Retired NFL linebacker Lawrence Taylor declared bankruptcy in the late 1990s despite racking up an estimated $50 million in career earnings. Taylor literally blew through his millions — he had a serious drug habit and had been arrested for drug possession several times, Complex reported. He also told “60 Minutes” that he spent about $1,000 daily on escort services.

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21/25

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Dermontti Dawson: Lost $70 Million in Bad Real Estate Investments

Former Steelers center Dermontti Dawson filed for bankruptcy in 2010, citing liabilities totaling nearly $70 million and assets of just $1.4 million, NBC Sports reported. Much of the debt was owed to business partners, primarily in real estate investments.

“Today’s real estate market and economic conditions, plus the fact that I own non-controlling minority interests in the entities which own the real estate, left me with limited options,” Dawson told NBC Sports at the time. “I certainly wish things had turned out differently.”

22/25

Tony Gutierrez/AP / Shutterstock.com

Terrell Owens: Lost $80 Million in Risky Investments and Real Estate

When Terrell Owens appeared on “Dr. Phil” in 2012, he admitted that he had lost all of the $80 million to $100 million he had earned over the course of his NFL career. But unlike other athletes who went broke spending on flashy cars and mega-mansions, Owens told GQ that his biggest financial mistake was being too trusting of others who advised him where to invest his millions. A series of risky investments and real estate holdings that lost their value after the 2008 market collapse are what led to the loss of his large fortune, he told the magazine.

23/25

Marcio Jose Sanchez/AP / Shutterstock.com

Tiger Woods: Lost $100 Million in His Divorce

Golf pro Tiger Woods’ very public divorce from Elin Nordegren ended with a very pricey settlement. Sources with direct knowledge of the property settlement agreement told TMZ that Nordegren would be walking away with close to $100 million. Fortunately, that’s just a drop in the bucket for Woods, who has earned $1.4 billion in sponsorship money alone since going pro in 1996, Forbes reported.

24/25

Paul Connors/AP / Shutterstock.com

Antoine Walker: Wasted $110 Million on Gambling and Excess

NBA player Antoine Walker declared personal bankruptcy in 2010 after spending or losing all $110 million of his career earnings, plus additional millions he had earned from endorsement deals. According to Sports Illustrated, Walker lost all his cash due to his lavish lifestyle, bad real estate deals, gambling losses and financially supporting his friends and family. The magazine reports that he once had 30 to 70 friends and family members on his payroll.

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25/25

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Allen Iverson: Blew $154 Million on a Personal Hairstylist, Jewelry and Entertaining His Entourage

NBA star Allen Iverson racked up estimated career earnings totaling $154 million, but despite that, it became widely reported that he was either broke or in debt after a judge ruled in 2012 that his checking account would be garnished after he failed to pay back $662,540 in debt and interest that he owed a jeweler.

Philadelphia Inquirer reporter Bill Lyon shared that he wouldn’t be surprised if Iverson had really blown through his nine-figure fortune, as he had witnessed firsthand how the athlete had spent money on a personal hairstylist who traveled with him to games, multiple excursions to the jeweler and entertainment for his numerous hangers-on.

About the Author

Gabrielle joined GOBankingRates in 2017 and brings with her a decade of experience in the journalism industry. Before joining the team, she was a staff writer-reporter for People Magazine and People.com. Her work has also appeared on E! Online, Us Weekly, Patch, Sweety High and Discover Los Angeles, and she has been featured on “Good Morning America” as a celebrity news expert.

Professional athletes can make millions of dollars through lucrative contracts — and sometimes billions when you add in endorsement deals — but despite their high paychecks, many end up going broke. According to a 2009 report by Sports Illustrated, 78% of former NFL players have gone bankrupt or are under financial stress within two years of retirement, and within five years of retirement, an estimated 60% of former NBA players are broke. Similar fates have befallen professional baseball, golf and hockey players as well.

But where exactly do those millions go? GOBankingRates is breaking down exactly how 25 athletes lost millions of dollars, with some falling from the top of their game to financial rock bottom.

Last updated: Feb. 6, 2020

Jim Prisching/AP / Shutterstock.com

1. Lance Briggs: Lost His $2.3 Million Illinois Mansion

Former Chicago Bears linebacker Lance Briggs spent 12 years playing in the NFL, retiring in 2015. Back in 2008, Briggs paid $2.3 million for a six-bedroom, 5,158-square-foot, English-style mansion in Northfield, Illinois, but lost it after his lender foreclosed on it in 2017, the Chicago Tribune reported. Briggs also owned a townhouse that went into foreclosure that same year, Crain’s Chicago Business reported.

The mansion was sold in January 2020 for $1.1 million — less than half what Briggs had purchased it for.

Paul Sancya/AP / Shutterstock.com

2. Clinton Portis: Lost $3.1 Million Due to Bad Financial Advice

Former Washington Redskins and Denver Broncos running back Clinton Portis signed an eight-year, $50.5 million contract in 2004, which at the time made him the highest-paid running back in NFL history, Sports Illustrated reported. But Portis filed for Chapter 11 bankruptcy and was basically broke by 2009. Portis told Sports Illustrated that trusting the wrong people was a major contributor to his financial downfall. His financial advisor, Jeff Rubin, got him to invest $1 million in an Alabama casino that was shut down in 2012 after the state’s regulators got involved. Portis told the magazine that a total of $3.1 million from his account was taken by Rubin.

“The complication begins because you don’t understand it,” he said. “You don’t know what they’re saying, but you just get involved.”

Shawn Thew/EPA / Shutterstock.com

3. Michael Vick: Lost $3.75 Million Due to Illegal Dogfights

When former NFL quarterback Michael Vick pleaded guilty to federal charges relating to an illegal dogfighting operation, the Atlanta Falcons sought to recover nearly $20 million in bonus money they had paid him between 2004 to 2007. The Falcons argued that Vick had used the money to finance his illicit activities. In 2008, a judge ruled that he could keep all but $3.75 million of the bonus money, ruling that recovering all of the bonuses would violate the NFL collective bargaining agreement, ESPN reported.

Vick ended up filing for bankruptcy in 2008, but by 2017, he had paid back $17.4 million of the $17.6 million he owed creditors. He was able to make the money back after rejoining the NFL and later working as a studio analyst for Fox Sports following his stint in prison.

AP / Shutterstock.com

4. Johnny Unitas: Lost $4 Million on an Investment in a Circuit Board Company

Former Baltimore Colt quarterback Johnny Unitas made a bad investment that landed him in bankruptcy court. The NFL player filed for Chapter 11 bankruptcy in 1991 after his bank attempted to collect on nearly $4 million in failed loans made to Unitas and his business partners in the mid-1980s for the purchase of a circuit board manufacturing company, The Baltimore Sun reported. According to Forbes, Unitas and his partners purchased National Circuits for $3.5 million in 1994, and six years later, they could only sell it for $1 million.

Anonymous/AP / Shutterstock.com

5. Jack Clark: Racked Up $6.7 Million in Debt With His Penchant for Fancy Cars

Former Boston Red Sox player Jack Clark — nicknamed Jack the Ripper — played in the MLB from 1975 to 1992 and filed for bankruptcy that same year, citing $6.7 million in debt. It’s likely his affinity for luxury cars landed him in the hole — his bankruptcy filing stated that he owned 18 cars, including a $717,000 Ferrari, Sports Illustrated reported.

AP / Shutterstock.com

6. Bryan Trottier: Racked Up $9.5 Million in Debt With a Failed Ice-Rink Business

Six-time Stanley Cup championship winner Bryan Trottier declared bankruptcy in 1994, with less than $150,000 in assets and nearly $9.5 million in debts. Some of those debts were owed to investors in his ice-rink business, BT Skating Corp., which went into foreclosure, The New York Times reported.

Mark J Terrill/AP / Shutterstock.com

7. Evander Holyfield: Lost His $10 Million Mega-Mansion

Boxer Evander Holyfield was once the proud owner of a 109-room, mega-mansion in suburban Atlanta, but the home was repossessed by the bank after he failed to make payments on his $10 million home loan, CNBC reported.

The house was eventually sold to rap mogul Rick Ross for just a fraction of what it cost Holyfield. The property was originally listed for $8.5 million but sold for less than $5.9 million, Redfin reported.

8. Luther Elliss: Lost $11.6 Million Due to Failed Investments and Overspending

Luther Elliss played 10 years in the NFL and made $11.6 million in one five-year span. But in 2010 he was relying on help from his church friends to pay his bills and even afford food, the Deseret News reported. He filed for bankruptcy in 2009 with a number of things attributing to his debt, including a $1.6 million mortgage loan and overspending on cars and jewelry. However, Elliss told the Deseret News that poor business decisions were the biggest culprit in his multimillion-dollar loss.

“Most of it was bad investments, good money chasing bad money, trying to save it instead of cutting your losses,” he said. “I’m not one to give up too easily on things, so it was always just a little bit more, a little more time, a little more money and before we knew it, I put up the houses and guaranteed the loans, and when that came due, the bank came knocking on my door.”

Gary I Rothstein/AP / Shutterstock.com

9. Dan Marino: Lost Over $13 Million on an Investment in the Company That Created the Tupac Hologram

Former Dolphins player and NFL analyst Dan Marino had a big stake — to the tune of 1.6 million shares — in Digital Domain Media Group, a digital production company founded by James Cameron that produced the digital effects for “Titanic” and “Transformers,” as well as the Tupac hologram that appeared at Coachella. His investment, which was once worth $14 million, dropped down to a value of $850,000 after the company declared bankruptcy, Sports Grid reported.

Markson Sparks / Shutterstock.com

10. Mike Tyson: Racked Up $13.4 Million in IRS Debt

Former heavyweight champion Mike Tyson earned about $400 million over 20 years in and out of the ring, but he squandered his wealth with lavish spending on everything from jewelry to Siberian tigers, The New York Times reported. In 2003, he filed for Chapter 11 bankruptcy stating that he had racked up $23 million in debt. Included in that debt was a whopping $13.4 million he owed the IRS.

Uncredited/AP / Shutterstock.com

11. Bernie Kosar: Lost $15 Million Because He Put Too Much Trust in Friends and Family

When quarterback Bernie Kosar signed a $6 million contract with the Cleveland Browns in 1985, he entrusted his father to take care of his money. Kosar has said that his father used Kosar’s signing bonus to pay his own mortgage and buy cars. According to the book “Is There Life After Football?” Kosar ended up losing $15 million between his father’s mismanagement of his funds, loans he gave to friends and family that were never paid back and bad investments he made that were spearheaded by friends and family.

BPI / Shutterstock.com

12. Floyd Mayweather: Racked Up $22.2 Million in IRS Debt

Mike Tyson isn’t the only boxer who ended up owing the IRS millions. Floyd Mayweather may call himself “Money,” but he didn’t have enough of it to pay the IRS what he owed in taxes — at least that’s what he claimed in response to a lien the IRS issued in 2015, Deadspin reported. Despite earning $200 million for a single fight, Mayweather asked the IRS for an extension to pay back the $22.2 million he owed them in taxes for the year.

Ann Heisenfelt/AP / Shutterstock.com

13. Vince Young: Lost $25 Million Through Negligence and Irresponsible Spending

NFL quarterback Vince Young signed a lucrative $25 million contract with the Tennessee Titans, but just seven years after he inked that deal he filed for Chapter 11 bankruptcy, Sports Illustrated reported. According to court documents obtained by the publication, Young’s assets totaled between $500,001 and $1 million, while his total debt was between $1,001,000 and $10 million.

Young said he didn’t pay attention to where his money was going throughout his career, trusting his financial advisor and his uncle to make decisions for him. He was also generous to a fault, purchasing one relative two cars, building a house for his mom and treating his teammates to a $15,000 meal at the Cheesecake Factory.

Matt Slocum/AP / Shutterstock.com

14. Jack Johnson: His Parents Spent His $30.5 Million Salary Before He Even Got It

NHL player Jack Johnson signed a seven-year, $30.5 million contract with the Columbus Blue Jackets, but was left with nothing and forced to declare bankruptcy after his parents mismanaged his funds. According to court documents, his parents took out loans against his future earnings, including at least $15 million across 18 high-interest loans that resulted in multiple defaults. His parents also allegedly purchased a beach house in California, bought cars and paid for travel to see him play, Forbes reported. Johnson was not aware of all the purchases made in his name and was sued several times for defaulting on loan payments.

David Richard/AP / Shutterstock.com

15. Warren Sapp: Spent His $40 Million Fortune on Shoes, Watches and a Lion-Skin Rug

Warren Sapp played in the NFL for 13 years, making an estimated $40 million over the course of his career, Bleacher Report reported. Not only did Sapp spend his fortune, but he ended up $6.7 million in debt, according to a bankruptcy filing he made in 2012. Overspending seems to be the cause of Sapp’s financial downfall — a list of his assets included 240 pairs of Jordan shoes worth over $6,000, a watch worth $2,250 and a lion-skin rug worth $1,200.

David Zalubowski/AP / Shutterstock.com

16. Mark Brunell: Sunk $50 Million in Failed Businesses

Former NFL player Mark Brunell lost the $50 million he earned throughout his career by putting it into failed businesses. Action News in Jacksonville, Florida, reported that he invested his money into nine businesses and enterprises, five of which went bankrupt. One of Brunell’s biggest financial losers was a company called Champion LLC, which purchased high-end investment properties. When the real estate market crashed, Brunell lost everything he had put into the company and ended up owing even more due to the loans that had been taken out to buy the properties.

17. John Daly: Gambled Away $50 Million

Golfer John Daly loves to gamble, a hobby that’s cost him millions. Daly told ESPN that he did the math on the shocking amount he’s lost: “I lost about $98 million and won about $45 million gambling. So yeah I lost around $50 million,” he said, according to USA Today.

Steven Senne/AP / Shutterstock.com

18. Curt Schilling: Lost $50 Million on a Gaming Company Investment

MLB pitching great Curt Schilling invested more than $50 million of his career earnings into his video game company, 38 Studios, and lost it all when the company declared bankruptcy in 2012, ABC News reported.

“The money that I had earned and saved in baseball was all gone,” he told radio station WEEI-FM. “I put everything in my name in this company. I believed in it. But I’m not asking for sympathy. That was my choice.”

Julie Jacobson/AP / Shutterstock.com

19. Sheryl Swoopes: Lost $50 Million Due to Bad Representation and Bad Investments

Although WNBA salaries topped out at six-figures when Sheryl Swoopes was in the league, she was able to make $50 million during her basketball career thanks to a lucrative Nike contract. Unfortunately, she lost it all due to a series of bad investments and poor money management by her lawyers and agents, Money reported. She filed for Chapter 13 bankruptcy in 2004.

Chris O'Meara/AP / Shutterstock.com

20. Lawrence Taylor: Lost $50 Million Due to Hard Partying and Drug Use

Retired NFL linebacker Lawrence Taylor declared bankruptcy in the late 1990s despite racking up an estimated $50 million in career earnings. Taylor literally blew through his millions — he had a serious drug habit and had been arrested for drug possession several times, Complex reported. He also told “60 Minutes” that he spent about $1,000 daily on escort services.

Gene J Puskar/AP / Shutterstock.com

21. Dermontti Dawson: Lost $70 Million in Bad Real Estate Investments

Former Steelers center Dermontti Dawson filed for bankruptcy in 2010, citing liabilities totaling nearly $70 million and assets of just $1.4 million, NBC Sports reported. Much of the debt was owed to business partners, primarily in real estate investments.

“Today’s real estate market and economic conditions, plus the fact that I own non-controlling minority interests in the entities which own the real estate, left me with limited options,” Dawson told NBC Sports at the time. “I certainly wish things had turned out differently.”

Tony Gutierrez/AP / Shutterstock.com

22. Terrell Owens: Lost $80 Million in Risky Investments and Real Estate

When Terrell Owens appeared on “Dr. Phil” in 2012, he admitted that he had lost all of the $80 million to $100 million he had earned over the course of his NFL career. But unlike other athletes who went broke spending on flashy cars and mega-mansions, Owens told GQ that his biggest financial mistake was being too trusting of others who advised him where to invest his millions. A series of risky investments and real estate holdings that lost their value after the 2008 market collapse are what led to the loss of his large fortune, he told the magazine.

Marcio Jose Sanchez/AP / Shutterstock.com

23. Tiger Woods: Lost $100 Million in His Divorce

Golf pro Tiger Woods’ very public divorce from Elin Nordegren ended with a very pricey settlement. Sources with direct knowledge of the property settlement agreement told TMZ that Nordegren would be walking away with close to $100 million. Fortunately, that’s just a drop in the bucket for Woods, who has earned $1.4 billion in sponsorship money alone since going pro in 1996, Forbes reported.

Paul Connors/AP / Shutterstock.com

24. Antoine Walker: Wasted $110 Million on Gambling and Excess

NBA player Antoine Walker declared personal bankruptcy in 2010 after spending or losing all $110 million of his career earnings, plus additional millions he had earned from endorsement deals. According to Sports Illustrated, Walker lost all his cash due to his lavish lifestyle, bad real estate deals, gambling losses and financially supporting his friends and family. The magazine reports that he once had 30 to 70 friends and family members on his payroll.

Paul Sancya/AP / Shutterstock.com

25. Allen Iverson: Blew $154 Million on a Personal Hairstylist, Jewelry and Entertaining His Entourage

NBA star Allen Iverson racked up estimated career earnings totaling $154 million, but despite that, it became widely reported that he was either broke or in debt after a judge ruled in 2012 that his checking account would be garnished after he failed to pay back $662,540 in debt and interest that he owed a jeweler.

Philadelphia Inquirer reporter Bill Lyon shared that he wouldn’t be surprised if Iverson had really blown through his nine-figure fortune, as he had witnessed firsthand how the athlete had spent money on a personal hairstylist who traveled with him to games, multiple excursions to the jeweler and entertainment for his numerous hangers-on.

About the Author

Gabrielle joined GOBankingRates in 2017 and brings with her a decade of experience in the journalism industry. Before joining the team, she was a staff writer-reporter for People Magazine and People.com. Her work has also appeared on E! Online, Us Weekly, Patch, Sweety High and Discover Los Angeles, and she has been featured on “Good Morning America” as a celebrity news expert.

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